Taxes — Page 5 — My Money Blog

ETF Tax-Loss Harvesting: 70% Overlap Rule of Thumb for Substantially Identical

December 26, 2016 By Jonathan Ping 2 Comments

calc_10key Tax-loss harvesting (TLH) is a common practice used to improve after-tax returns by realizing losses to either offset realized capital gains or to defer capital gains into the future. Many robo-advisors including Betterment and Wealthfront offer automated tax-loss harvesting as a feature. As nearly all of them hold ETFs, they accomplish this by selling the primary ETF for each asset class and replacing it temporarily with an alternative, secondary ETF. DIY investors can perform a similar maneuver as well.

The IRS wash sale rule states that you can’t deduct a loss by selling a security and immediately replacing it with something “substantially identical”. Instead, harvesters buy an ETF that is slightly different. It’s a grey area, as there is no solid definition of what “substantially identical” means. However, this recent Barron’s article (paywall, use Google News) offered up a rough rule of thumb that I hadn’t seen before (bolding mine):

Although the wash-sale rule remains ambiguous, there may be an alternative standard that investors can use for guidance. In the 1980s, the IRS created the “straddle rules” to address a loophole in hedged long-short portfolios. For tax-loss purposes, the portfolios on the long side couldn’t be “substantially similar” to those on the short, which the IRS defined as having over 70% overlap. “Some people use the straddle-rules definition as a surrogate to apply to the wash-sale rule,” says Eric Fox, a principal at Deloitte Tax. “If two ETFs don’t have more than 70% overlap and they’re not substantially similar, how could they ever be considered substantially identical?” That should give loss harvesters some confidence.

I was surprised by the conservativeness of this rule of thumb. Most of the TLH articles I have read by both human and software-based advisors implement more aggressive strategies than the 70% maximum overlap suggested above. A traditional advisor quoted in the Barron’s article admitted swapping between the Vanguard Total International Stock ETF (VXUS) and the Vanguard FTSE All-World ex-US ETF (VEU). VXUS and VEU have a 76% overlap by weight, according to this ETFResearchCenter.com Overlap Tool:

etf_tax1

Perhaps more importantly, these two ETFs have a near 100% performance correlation. Here’s a chart of the two ETFs over the last 12 months, per Morningstar (click to enlarge):

Meanwhile, this Wealthfront whitepaper shows their ETF tax-loss pairings and their correlations. Out of the 7 pairs, 4 have correlations of 97%+ and all of them are over 70%.

etf_tax3

Commentary. There are few firm answers here. If robo-advisors marketing aggressive ETF tax-loss harvesting gather a lot of assets, I suspect the IRS will eventually provide additional guidance. I imagine the worst-case scenario as the IRS classifying past trades as violating the wash sale rule, nullifying your tax losses and possibly imposing additional penalties. I guess current practitioners don’t see a big risk of that happening. They essentially see a nearly free lunch by substituting these similar ETFs. Still, when you market something publicly as 99% correlated, aren’t you basically admitting that they are “substantially identical”?

Filed Under: Investing, Taxes

Last updated: December 26, 2016

My Money Blog has partnered with CardRatings and may receive a commission from card issuers. Some or all of the card offers that appear on this site are from advertisers and may impact how and where card products appear on the site. MyMoneyBlog.com does not include all card companies or all available card offers. All opinions expressed are the author’s alone, and has not been provided nor approved by any of the companies mentioned.

MyMoneyBlog.com is also a member of the Amazon Associate Program, and if you click through to Amazon and make a purchase, I may earn a small commission. Thank you for your support.

Credit Karma Tax 2019: $0 Federal and $0 State Tax Filing w/ No Last-Minute Charges

December 12, 2016 By Jonathan Ping 22 Comments

Tax season is officially here and the IRS is accepting E-files. For you early birds, Credit Karma Tax is now on its 4th year of offering 100% free Federal AND State tax preparation software with free e-File and no income restrictions. You can have itemized deductions, business income, self-employment tax, and/or capital gains and losses. They now also have a Max Refund Guarantee, Accurate Calculations Guarantee, and Audit Defense include if you get audited.

My favorite feature of this product is that there is no “upgrade” version, so there are no upsells and no last-minute fees. Your bill will always be $0 Federal, $0 State. I hate the feeling when you have spent hours (days?!) typing in all that data and you expect a certain price, but then at the very end they want to charge you a little bit more. You are just too tired to do it all over again, so you accept, but it leaves a bad taste in your mouth.

Is this legit? What’s the catch? Yes, they are legit. Credit Karma purchased AFJC Corporation, which was a private-label software provider and previously supplied the online tax software for Jackson Hewitt. They’ve been running this offer since 2016.

The “catch” is that you must also sign up for the main CreditKarma.com site, which takes your personal information and provides you access to your credit scores and reports from two of the three major consumer credit bureaus. They make money by also using that personal information to show you customized advertisements for things like credit cards, banking, and insurance products.

What’s included.

Free Federal filing with free e-File for 90%+ of filers with no income restrictions.
Free State filing for 40 states + Washington DC. (Some states don’t have income tax).
No upsells, no upgrades, no “premium version”.
You can print and snail mail if you choose not to e-File.

Here are some popular forms included by Credit Karma Tax that other “Free” editions probably don’t cover:

Schedule C – Profit or Loss from Business (Sole Proprietorship)
Schedule D – Capital Gains and Losses (Stock Sales)
Schedule E – Supplemental Income and Loss (Rental property)
Schedule SE – Self-employment tax

What’s NOT included. Credit Karma will NOT support the following forms this year:

Multiple state filings
Part-year state filing
Foreign earned income
State returns for married filing separately in community property states*
State filing without a federal filing

No business tax returns. Credit Karma Tax supports Sole Proprietorships and income reportable on a Schedule C/E/SE, but does NOT yet support business tax returns for an S corporation, C corporation, partnership or multi-member LLC.

Tell me more about how Credit Karma makes money. Quoted from their site:

When you visit Credit Karma, we show you offers and recommendations (like credit cards or loans) that could save you money. If you take one of these offers, the bank or lender usually pays us. We never charge you a dime. And we never sell your info to marketers.

For example, if they know you have a 4% rate mortgage, they could sell you a 3.5% refinance mortgage. If they know you are older and have a paid-off home (i.e. you pay property taxes but no claim no mortgage interest), they could sell you a reverse mortgage. If they know your income, they can estimate the amount of life insurance you need. You could actually like this customization, be creeped out completely, or simply plan to ignore the ads.

Try before you commit. Nearly all the online tax prep software only bills you when you are ready to file. If you’re not sold on a single product, why not sign up and do this and a competitor side-by-side in two different browser tabs. It’s a bit more work, but not a lot if you’re doing it simultaneously. That way, you can double-check the calculations. Ideally, you should get the same refund/due amount for both and then you can file for free!

Bottom line. Credit Karma Tax will give you free Federal and State tax returns. There is no other version, so you will never be hit with a last-minute upcharge. In exchange, you let them show you ads based on your financial data. In terms of technical accuracy, I expect that they are roughly equal to the other major providers. However, you may value the convenience factors offered by competitors (easily import last year’s data, unlimited phone support, automatic import of 1099-B tax lot data).

Filed Under: Deals & Offers, Taxes

Last updated: January 28, 2020

Mortgages, Imputed Rent, and Early Retirement

May 3, 2016 By Jonathan Ping 15 Comments

mcman286 In a Quora question What do economists think about buying vs renting a house?, in addition to the previously-mentioned answer by Alex Tabarrok of Marginal Revolution, there was another well-ranked answer by Erik Brynjolfsson, professor at MIT Sloan. One of his three points was about the value of imputed rent (read the other ones as well):

Second, there’s a huge tax benefit to housing which comes from the hidden “dividend” it pays. I’m not talking (just) about the (too) generous mortgage deduction, but rather the fact that you don’t have to pay taxes on the implicit rent you earn on your house since its paid to yourself. A house generates enormous rental value each month — like a dividend. If you rent it to yourself, you take the money out of one pocket and pay it to the other one, and the IRS doesn’t tax that. In contrast, if you earn money some other way and then use that money to pay rent, you probably also have to pay taxes. That can add up.

From the Wikipedia entry on imputed rent:

Consider a model: two people, A and B, each of whom owns property. If A lives in B’s property, and B lives in A’s, two financial transactions take place: each pays rent to the other. But if A and B are both owner-occupiers, no money changes hands even though the same economic relationships exists; there are still two owners and two occupiers, but the transactions between them no longer go through the market. The amount that would have changed hands had the owner and occupier been different persons is called the imputed rent.

In other words, as a homeowner you could be considered both the landlord and the renter. Let’s say you would rent your house for $1,600 a month. If you were in the 25% marginal tax bracket, you have to earn $2,133 a month pre-tax to cover that rent (and pay $533 in income tax).

As part of my “rough model” of early retirement, I recommend setting your mortgage payoff date to coincide with your retirement date (for those that choose to buy a home). Part of the reason for that is that you won’t have to generate that extra income to pay your mortgage anymore. This could lower your marginal tax bracket into the next lower bracket, and also the tax rate on your capital gains.

For example, $1,600 in monthly rent equates to nearly $20,000 a year in after-tax expense, or nearly $26,000 in gross income at the 25% tax bracket. Here are the 2016 federal income tax rates (source):

2016taxschwab

Ideally, I would target my household expenses to stay in the 15% tax bracket for married joint filers in retirement. Being able to reduce my taxable income by over $25,000 would definitely help someone stay in the 15% tax bracket range. Also, if you are the in 15% ordinary income tax bracket, your tax rate on qualified dividends and long-term capital gains becomes zero!

Now, the idea of imputed income could be extended further. When I cook at home, I save the money from eating out an Applebee’s. Let’s say a dinner out costs $40 for the family. To reach $40 after-tax, I’d have to generate $53 of income at a 25% tax rate. Same with childcare, housekeeping, laundry, yard maintenance, etc. But housing is an area with significant impact, usually the biggest item in a household budget.

Filed Under: Real Estate, Retirement, Taxes

Last updated: May 3, 2016

IRS Estimated Taxes Due Dates 2016

March 28, 2016 By Jonathan Ping 14 Comments

irsclip If you have self-employment or other income outside of your W-2 paycheck this year, you may need to send the IRS some money before the usual tax-filing time. Here are the due dates for paying quarterly estimated taxes in 2016; they are supposed to be in four equal installments. This is for federal taxes only, state and local tax due dates may be different.

IRS Estimated Tax Payment Calendar for Individuals

Tax Year / Quarter	Due Date
2016 First Quarter	April 18, 2016 (Monday)
2016 Second Quarter	June 15, 2016 (Wednesday)
2016 Third Quarter	September 15, 2016 (Thursday)
2016 Fourth Quarter	January 17, 2017* (Tuesday)

* You do not have to make the Q4 payment due January 17, 2017, if you file your 2016 tax return by January 31, 2017 and pay the entire balance due with your return.

Who needs to pay estimated taxes?
In general, you must pay estimated tax for 2016 if both of the following apply:

You expect to owe at least $1,000 in tax for 2016, after subtracting your withholding and refundable credits.
You expect your withholding and credits to be less than the smaller of
- 90% of the tax to be shown on your 2016 tax return, or
- 100% of the tax shown on your 2015 tax return. Your 2015 tax return must cover all 12 months.

If you forget to pay (like I’ve done before), then you should make a payment as soon as possible even though it is late. This will minimize any penalty assessed.

How do I pay? When does the payment count?

By check. Fill out the appropriate IRS Form 1040-ES voucher (last page of the PDF) and snail mail to the indicated address. The date of the U.S. postmark is considered the date of payment. No fees besides postage.
By online bank transfer. You can store your bank account information and pay via electronic funds transfer at EFTPS.gov or call 1-800-555-4477. It takes a little while to set up an online account initially, so you’ll need to plan ahead. For a quick one-time payment, you can also use IRS Direct Pay (just introduced in 2014) which does not require a sign-up but it also doesn’t store your bank account information for future payments. Both are free, there are no convenience fees. The date of payment will be noted online.
By debit or credit card. Here is page of IRS-approved payment processors. Pay by phone or online. Fees will apply, but the payment will count as paid as soon as you charge the card. You may also earn rewards on your credit card. Check if there is a discounted fee available via limited-time promotion.

How much should you pay in estimated taxes? You’ll need to come up with an expected gross income and then estimate your taxes, deductions, and credits for the year. The PDF of Form 1040-ES includes a paper worksheet to calculate how much in quarterly estimated taxes you should pay. You can also try online tax calculators like this one from H&R Block to estimate your 2016 tax liability, and divide by four quarters.

Filed Under: Entrepreneurial, Self-Employment, Taxes

Last updated: March 28, 2016

Pay Taxes With Credit Card: Lowest Fee Rates and Limited-Time Promotions

March 21, 2016 By Jonathan Ping 16 Comments

1040clip We all know that personal income tax filings are due soon, but so are the first round of quarterly estimated taxes for 2016. Many of us with freelance or side-gig income must makes these payments in order to avoid a tax penalty at the end of the year.

You can pay taxes with a credit card, but there is usually a convenience fee attached. So why would you bother?

You may wish to earn rewards for the purchase in the form of cash back, points, or miles. These rewards may be of greater value to you than the fee. (* See bottom of post for examples.)
You may want to pay off the balance more gradually, especially if you have a low interest rate offer like 0% for 12 months on purchases.

Here I’d like to keep track of the current rates for convenience fees, any limited-time promotions, as well as some credit card with rewards greater than the convenience fees.

Limited-time offer: 1.75% fee with Mastercard from Plastiq. I received an e-mail from Plastiq stating:

Taxes are due in less than a month, so make it easier on yourself by paying them through Plastiq. To make taxes even less painful, we’re offering a special promotion starting today. Get a 1.75% rate for all federal and state tax payments when you use your MasterCard!*

So get ahead of the game and pay your taxes now. This special rate will expire on April 18, 2016 a 5 p.m. PT, so sign in and take full advantage of this limited-time offer!

There is no landing page, but the offer is mentioned on their Twitter so I assume it is not targeted. You must initiate your purchase from this link, which ensures that you can only use the offer to pay federal or state taxes. The sub-categories include income taxes, payroll withholding taxes, self-employment taxes, business taxes, and more.

Standard convenience fee rates for 2016 start at 1.87%.

The IRS keeps a list of approved payment processors and updates it regularly. Here is the list, along with fees valid until December 31st, 2016. All of them accept Visa, Mastercard, Discover, and American Express.

Pay1040.com: 1.87% fee with a minimum fee of $2.59
PayUSATax.com: 1.99% fee with a minimum fee of $2.69
OfficialPayments.com: 2.25% fee with a minimum fee of $2.50

Note that there is a frequency limit on how often you can make credit card payments. You can make credit card payments towards estimated taxes up to twice per quarter.

Screenshot:

irstaxcredit2

Are the fees tax-deductible? You may also want to take into consideration that the convenience fee may be tax-deductible or a business expense:

The fee is deductible for personal tax types as a miscellaneous itemized deduction. However, only those miscellaneous expenses that exceed 2% of adjusted gross income can be deducted. For more information, see IRS Publication 529.
For business tax types, the fee is a deductible business expense.

Personal experiences. I have used Plastiq to make credit card payments (though not tax payments yet), and I have used PayUSATax.com back when they were the cheapest option. Both experiences were positive with no issues. Your credit card statement will list this payment as “United States Treasury Tax Payment.” The convenience fee will be listed as “Tax Payment Convenience Fee” or something similar. Here’s what my statement looked like:

irstaxcredit3

Notably, I know of no reason why you would not just go with the cheapest available payment processor. If they are on the IRS list, they are all officially accepted by the IRS. In fact, in my testing I found the most expensive one to offer the worst in-browser user experience.

To avoid any headaches, I would take great care when making the payments to make sure they are properly designated, as the payments are not reversible or refundable by the processor.

Specific credit card examples. The following cards currently have the ability to offer cash back rewards equal or greater than 1.75%, meaning you can actually make money by paying your taxes with them. Please read my card-specific reviews for details.

Filed Under: Credit Cards, Taxes

Last updated: February 9, 2017

TurboTax vs. TaxACT vs. H&R Block Online 2016 Lightning Review

March 7, 2016 By Jonathan Ping 16 Comments

1040clip For the last few years, I’ve completed my personal returns top-to-bottom using each of the three most popular online tax prep providers – TurboTax, H&R Block, and TaxACT. I started my 2015 tax year returns this weekend, but each one was close enough to last year’s experience that I couldn’t bring myself to do all that repetitive data entry again. I did run through the major categories, explored the import features, and tried contacting their customer support.

The major differentiating factors remain price, time-saving features, audit support, and ability to answer specific tax questions. All three offer a “Maximum Refund Guarantee” (relative to competing software) as well as an “Accuracy Guarantee” (relative to your tax bill or refund amount) that says that they will pay any penalty and interest assessed by the IRS or your state due to calculation errors on their part (though H&R Block limits this to $10,000). Actual cost can vary widely with sales and discounts, listed here are just the everyday prices. My condensed review:

TurboTax Online

Most expensive. Federal Deluxe regular price is $34.99 w/ e-file and supports itemized deductions. However, you need Premier at $54.99 if you have an investment gains or rental property. State return price is $36.99.
Best import features. Imports a lot of information from last year’s return. Automatically imports W-2s from many payroll providers and (by far the most) 1099 forms directly from financial institutions, both saving time and improving accuracy. Works with free “ItsDeductible” program to help with recording charitable donations.
Moderate audit support. You get help, but no in-person representation.
Moderate tax advice – You can request a phone call-back, wait time given upfront (10 minutes for me). Good online question database.
Annoying upsells. Intuit always feels like they are trying to extract the most money out of you.

Bottom line: The time-saving choice if you have a lot of brokerage transactions, W-2s, or other 1099 forms to electronically import this year. Also if you have a lot of details to import from last year’s return with TurboTax. It may be worth the extra cost to avoid tedious data entry.

TaxACT Online

Least expensive. Federal Plus regular price is $19.99 w/ e-file and supports itemized deductions, capital gains, and rental income. Federal + State return combined including e-file at $19.99.
Limited import support (worst of the three). Free Donation Assistant® feature to track charitable donations.
Limited audit support (worst of the three).
Limited tax advice quality (worst of the three). The hardest to find real person help. You can get phone support, but only if you pay first. Online question & answer database is available.

Bottom line: The value choice if you just want accurate DIY tax return software and don’t need any extra assistance.

H&R Block at Home Online

Middle-of-road pricing. Federal Deluxe regular price is $34.99, which supports itemized deductions and capital gains. You need Premium at $49.99 for rental property. State return price is $36.99.
Moderate import support for 1099s and W-2 (not as broad at TurboTax, better than TaxACT).
Best free audit support. Only product that includes an H&R Block Enrolled Agent actually attending your audit in-person. However, consider whether you would hire your own representative in the actual event of an IRS audit.
Easiest to get in-person tax advice. Free Live Chat included, wait time given upfront (4 minutes for me). Good online question database.

Bottom line: The most helpful choice if you don’t quite want to pay to person to do it all for you, but you are worried you might need some assistance. Based on overall experiences, H&R Block uses their brick-and-mortar experience to provide the best answers if you have tax questions. You also get the assurance that a federally-authorized enrolled agent will guide you for free through a potential albeit unlikely audit.

Tim Gray did his annual NY Times comparison as well, with very similar experiences to my own. As he puts it:

Each program’s maker has staked out a place in the market where it excels. TurboTax’s technology is the smoothest to use — the program rarely frustrates and offers a few features each year the competitors don’t match. Block’s tax help is the easiest to understand and get access to. TaxAct’s offerings are the cheapest.

I would add that although each product still has their strengths, this year the margins are getting closer. All three offer guidance throughout the filing process. In terms of price, TaxACT is still the cheapest but the total cost is higher than in previous years. In terms of online interface, all three are pretty similar, with TaxACT modernizing parts of their interview process. H&R Block remains best at one-on-one tax advice, but all three offer tax question databases (and really, there’s always Google for everything else). As the feature leader, TurboTax added a few more incremental things like a slick smartphone and iPad apps which you can use simultaneously with the traditional web browser version. Overall, the competition has made for slightly better products across the board.

All of these sites work on a “start for free” basis, so you can also try them out yourself before having to commit and pay anything.

Filed Under: Reviews, Taxes

Last updated: March 4, 2018

TurboTax Desktop Software 2015 Deals, 40% Off at Amazon

January 24, 2016 By Jonathan Ping 15 Comments

Tax prep season is coming up soon, and Amazon has some deals going on for desktop versions of Intuit TurboTax for Tax Year 2015. Here are some reasons that you may choose the desktop software version (CD or download) over their more-popular TurboTax.com online version:

With desktop software, you keep all your sensitive data (Social security number, income, etc.) on your own home computer instead of on someone else’s cloud server.
The desktop software allows up to 5 Federal tax returns (including 5 separate e-Files) per product purchase. So if you have extra family members or close friends, you can share it and save money.
Depending on the promotion, buying the download/CD version can be cheaper than using the online version. Note when comparing prices: If the download/CD version only says State download is included and not explicitly State e-File, then you can complete a state return, but the State e-File will be an additional cost of $19.99 per return. (By contrast, the TurboTax.com online version charges $36.99 for the state software add-on, but it includes one state e-File.) My suggestion is to simply print out your return, mail it in for the cost of a stamp and envelope, and pocket the savings.

There are two separate Amazon promotions going on right now. First, receive up to 40% off the desktop software versions of Intuit TurboTax 2015 (either Mac or PC, download or physical CD). You can get only Federal or Federal + State. Promotion link. Expires January 30th, 2016. Example prices:

TurboTax Deluxe 2015 CD/Download, Fed w/ E-File Only: $29.99. If you buy directly from Intuit, the price is $49.99.
TurboTax Deluxe 2015 CD/Download, Fed w/ E-File + State: $39.85. If you buy directly from Intuit, the price is $59.99.
TurboTax Premier 2015 CD/Download, Fed w/ E-File + State: $54.85. If you buy directly from Intuit, the price is $89.99.

Buy a bundle including both Intuit TurboTax and Quicken on CDs, and save $20 on the entire bundle. You have to add to cart and go to Checkout in order to see the discount. Note that this is physical CD only, but both Mac and PC versions are on the TurboTax CDs. However, Quicken for PC and Mac are different prices. Promotion link. Example prices:

(Note: Please verify prices, as they have been changing. Pretty annoying actually, as only the $20 off is set, but they keep changing the original price of the bundle instead.)

TurboTax Deluxe 2015 CD, Fed w/ E-File Only + Quicken Deluxe 2016 for PC Bundle = $59.84 – $20 discount = $39.84 for both.
TurboTax Deluxe 2015 CD, Fed w/ E-File + State + Quicken Deluxe 2016 for PC Bundle = $69.70 – $20 discount = $49.70 for both.
TurboTax Premier 2015 CD, Fed w/ E-File + State + Quicken Deluxe 2016 for PC Bundle = $84.70 – $20 = $64.70 for both.
TurboTax Premier 2015 CD, Fed w/ E-File + State + Quicken Deluxe 2016 for *Mac* Bundle = $104.84 – $20 = $84.84 for both.

At the time of writing this post, it works out to getting Quicken 2016 PC for about $10 extra. If you turned around and sold the Quicken on Amazon Marketplace or eBay, you’d probably get more than $10, which means your net price for TurboTax would be even lower than the first promotion (in exchange for some extra work).

Filed Under: Deals & Offers, Taxes

Last updated: April 25, 2019

How To Generate and Mail Your Own 1099-MISC Forms

January 13, 2016 By Jonathan Ping 19 Comments

1099blanks Did you as a small business pay another person or unincorporated business more than $600 total in the last year? You may have to provide them a 1099-MISC form.

Here are the specific rules as laid out in the official IRS Form 1099-MISC Instructions [pdf]:

The Internal Revenue Service (IRS) requires businesses (including not-for-profit organizations) to issue a Form 1099 to any individual or unincorporated business paid in excess of $600 per calendar year for services rendered. This is required whether these payments are spread out over the course of the year or are paid in one lump sum payment. The most effective way to obtain the information needed to prepare the Form 1099 is by requiring that an IRS Form W-9 be completed prior to any payment being made. The penalty for failure to file Form 1099 can be as much as 50% of the amount paid for services.

Note that last sentence: The penalty for failure to file Form 1099 can be as much as 50% of the amount paid for services.

The 1099-MISC forms must typically be sent out to independent contractors by January 31st following the end of the tax year in which you made the payments. You must also file a Form 1096 and submit the information to the IRS by March 31st.

If you’ve got your own accountant or payroll service, then you can pay them to generate the proper forms and send out these 1099s. However, I have done it myself as well, as it is not very difficult. Here are your options for generating and issuing a Form 1099:

You can order physical, blank 1099 forms from the IRS for free, but it may take 10 business days or longer (2+ weeks) to arrive. (It look closer to a month for me!) Here is the IRS.gov order page. You’ll need at a minimum, Form 1099-MISC and Form 1096. You then fill out and print both forms yourself and mail it out. Cost: Free.
You can order physical, blank 1099 forms online or from an office supply store. Here is the top-reviewed blank 1099-MISC kit from Amazon.com which includes multiple copies, envelopes, and 1096 forms. You then print it out yourself and mail it. Cost: ~$22 shipped for a kit of 25. You can get it with the printing software for about $35 shipped. This alternative brand includes online e-File instructions for about $16.
You can use a 3rd-party online service where you fill out the information online and they’ll create a PDF for you. The most popular is Intuit’s version (they make TurboTax). You will still need to print it out and mail the 1099 forms to your independent contractors, but they will e-file the information to the IRS. Cost: ~$15 for up to 3 forms, $4 each additional.
You can use 3rd-party tax prep software for businesses where you will be guided as with tax software as to how to fill out the appropriate forms. The most popular is TurboTax Business (not the personal edition), which will help you file your return and also generate both 1099-MISC and W-2 payroll forms for you. It comes with a 60-day money back guarantee from Intuit, so if it doesn’t work to your satisfaction, you can return it within 60 days for a full refund. Cost: ~$105 for tax filing software which includes unlimited 1099 and W-2 forms.

The easiest way would be to use a computer printer, but of course the IRS doesn’t make it that easy. In order to get the numbers “set” correctly for printing, you could be one of many free homemade templates out there (although I can’t vouch for any specific one as they may contain viruses or malware, etc). You can also buy forms + software packaged together to fill them out. Don’t forget to fill out the red copies for the IRS.

You can also fill out the official physical forms with a typewriter, or you can even handprint if you follow the IRS directions very carefully. Note that you cannot use the blank 1099 PDFs that you find online; they are only examples.

Finally, remember that your first job is to get a W-9 form [pdf] filled out by the person you paid, so that you’ll have their Tax ID to enter onto your tax forms.

Filed Under: Self-Employment, Taxes

Last updated: January 26, 2024

Home Improvement Receipts: Scan Now, Save Indefinitely

July 7, 2015 By Jonathan Ping 1 Comment

housecostbasis2 For many people, when they sell a home they don’t even consider taxes. But over time, especially if you live in a relatively expensive area, more and more people will bump up against the federal capital gains exclusions of $250,000 for individuals and $500,000 for couples. (You must have lived in the home for at least two out of the five years before the sale.)

This NY Times article projects that the following share of homeowners in certain high-cost cities will exceed the 250k/500k limits within the next 10 years, assuming just 3.5% annual growth and no further improvements. (Also consider the uncomfortable idea that you really can’t know if you’ll be single or married when it comes time to sell your home.)

housecostbasis

Most importantly, the article provides a good reminder to save all of your home-related receipts because they can raise your cost basis and thus reduce any potential capital gains. It’s so easy, and those little pieces of paper can literally be worth thousands of dollars down the road when the tax bill hits.

In general, you should save all of your home repair and remodeling receipts, although things considered maintenance won’t count (painting, fixing leaks, patching cracks, etc.). Here are a bunch of things taken from IRS Pub 523, Selling Your Home. Don’t take this as specific tax advice, but instead as a potential reminder in case you have done something on this list but don’t have the receipts properly stored away and archived.

Home Acquisition and Closing Costs.

Charges for installing utility services, legal fees for preparing the sales contract, title search fees, recording fees, survey fees, transfer or stamp taxes, and owner’s title insurance.

Home Improvements

Additions. Bedrooms, bathrooms, garages, decks, patios.
Exterior. New roof, siding, satellite dish, storm windows.
Interior. Built-in appliances, kitchen modernization, flooring, wall-to-wall carpeting, fireplace.
Lawns and grounds. New driveways, landscaping, fences, retaining walls, sprinkler system, swimming pools.
Systems. Heating, air conditioning, furnace, duct work, air/water filtration, security system.
Plumbing. Septic, water heater, water softener, water filtration.
Insulation. Attic, walls, floors, pipes, ductwork.

Physical receipts can get lost or fade over time, but the IRS accepts electronic records so it is quite easy to make a PDF using either your home scanner or just your smartphone. I use the well-reviewed Scanner Pro app and am impressed by its quality, but there are many competitors out there that I haven’t tried. You can then save to a cloud service like Dropbox or Evernote, or simply e-mail them to a searchable gmail account as another form of backup.

Filed Under: Frugal Living, Real Estate, Taxes

Last updated: July 7, 2015

Paperless vs. Paper Statements

May 20, 2015 By Jonathan Ping 23 Comments

Pictured above is the Fujitsu ScanSnap iX500 Scanner. It can digitize a page every 2 seconds, and some version of it has been on my Amazon Wishlist for many years. However, I still haven’t plunked down 400 bucks for it, because I don’t know if I’ll ever go completely paperless.

There are many tutorials on how to scan all your paper documents into Dropbox or Evernote. Liz Weston recently had a Reuters article about going paperless with tax-related documents:

I don’t make New Year’s resolutions. Instead, I resolve every tax season to get a better handle on my paperwork — with mixed results. This year, I turned to three certified public accountants to find out what apps, software and strategies they use to keep track of everything.

Kelley Long, a Chicago CPA and personal financial specialist, tries to generate as little paperwork as possible, opting for electronic records instead. “The IRS accepts electronic records,” said Long, resident financial adviser with Financial Finesse in Chicago. “There’s no need to keep paper. That’s the one thing they’re modern about.”

Long keeps a folder on her computer desktop for the current year’s tax documents. If a document comes to her in paper form, she scans it, saves it in the folder and shreds the original. She converts emails documenting charitable contributions and other tax-related expenses into PDF files by choosing the “print” function and then “save as PDF.” […] At the end of the year, she downloads her bank and credit card statements into the folder.

But then Reader Bill sent over this Clark Howard article about the benefits of paper statements:

If you think about all the companies you do business with, they all try to get you to turn off paper statements. If you’ve done so, I want you to turn that around and go back to getting statements in the mail.

With a paper statement in hand, it’s easier to prove that you had the money in the first place in the event funds go missing. If you are set up for electronic info only, well, that’s going to hurt. So the best precaution I can give is for you to go back to getting the paper.

So, which is safer? In my opinion, for most things they are equivalent. Paper statements can be lost, stolen, or destroyed (i.e. house fire). Electronic statements can be lost, hacked, or destroyed (i.e. hard drive crash). You can protect yourself with redundant copies of either one (i.e. safe deposit box, extra USB drive, cloud backup). Keeping a nice long history of either paper or paperless statement can help you prove ownership or status of assets. Indeed, the IRS accepts electronic copies as equivalent to paper, so why shouldn’t we?

(I would agree with the implication that those repeated calls for you to “go paperless” are less about eco-friendliness and more about saving printing and mailing costs. I am also curious to know if credit card companies have found that paperless statements lead to more missed payments and thus more interest and late fees. It certainly is less wasteful, though.)

The safest thing would be to keep both. In the event of some Fight Club-esque event where the digital records of your assets are lost, paper statements might help. In the event of some local disaster where my home and my bank is destroyed, then digital records in the cloud would be helpful. (It may be a good idea to read up on file encryption.)

What do I do? I maintain regular paper statements for my most important financial accounts. That’s basically my primary IRA, 401(k), brokerage, checking, and savings accounts. The main reason for the statements is that I am in charge of family finances, and if I am injured or worse, then my spouse will be able to track everything simply by opening up the mail (plus other estate documents). I also keep paper copies of our monthly bills coming in for the same reason. I still enjoy my ritual of sitting down with physical bills and paying my bills (online) once a month as I use the opportunity to review our monthly spending. Important statements are sent to a P.O. Box instead of my house to reduce chance of theft and protect privacy.

I also have several other financial accounts that are either dormant, temporarily opened for reviews or experiments, or have low balances. Those are all set to paperless and tracked online by Mint.com. I’d rather give Mint my passwords and keep a virtual eye on all of them, rather than the likely alternative of never checking in on them at all.

Filed Under: Simple Living, Taxes

Last updated: April 25, 2019

H&R Block Online Review – 2014 Tax Year Features and Screenshots

February 27, 2015 By Jonathan Ping 15 Comments

Here is my 2014 review of H&R Block Online DIY tax preparation software, to complement my TurboTax 2014 review and TaxACT 2014 review. I filed my personal tax return using each of the “Big 3” and I will try to share the overall experience along with their specific strengths and weaknesses.

Price
H&R Block Online comes in Free, Basic, Deluxe, and Premium tiers. Due to having stock sales but no self-employment deductions, I am going with H&R Block Deluxe Online which costs $29.99 for Federal and $36.99 for State (free state options may be available separately). I am reviewing the more popular online software, not the desktop download software which may be different both in user experience and price.

hrb2014_0

Tax Situation
Here’s a quick summary of our personal tax situation.

Married filing jointly, subject to state income tax
Both with W-2 income, as well as some simple 1099-MISC forms.
Interest income and dividend income from bank accounts, stocks, and bonds (Schedule B).
Contribute to retirement accounts (401ks and IRAs).
Capital gains and losses from brokerage accounts (Schedule D).
Itemized deductions (Schedule A), including property taxes and charitable giving.

User Interface and User Experience
In terms of overall visual feel, the 2014 user interface is clean and pleasant. If I was comparing with TurboTax and TaxACT, I would say H&R Block is a little less pleasing than TurboTax and a little more pleasing than TaxACT. All of them are perfectly acceptable, but that is my personal ranking. See screenshots throughout this review.

In terms of user experience, H&R Block also uses a question-and-answer format like other tax prep software, but I actually think they have the best layout for intermediate to advanced users (i.e. you’ve done your taxes online before). Before each major section (Income, Deductions, Credits), it present a long checklist of potential items to enter in. You just tick off the ones you need, instead of repeatedly reading a new screen for each little thing and clicking Yes, No, No, No, Yes, No, etc. It know it may sound insignificant, but it really does speed things up with everything on one screen. Here are partial screenshots to help explain:

Importing Data From Previous Years
You can pull up all of your old tax information for free from any of the Big 3 providers (H&R Block, TurboTax, TaxACT) as long as you are using Basic, Deluxe, or Premium (no Free). You may need to have the information downloaded in PDF format. You’ll get filing status, dependents, address, DOB, SSN, etc.

Importing W-2 and 1099 Forms Directly From Providers
Similar to TurboTax, H&R Block also automatically imports many W-2 and 1099 forms. You can pull up W-2 data using your employer’s tax ID number (EIN). My data point: the same W-2 that TurboTax imported, H&R Block did successfully as well (TaxAct could not).

H&R Block does not appear to publish a list of all their 1099 import partners, but I would say it is a little smaller than TurboTax and much more than the 6 partners that TaxACT supports. You just start typing the name and it tries to autocomplete if available:

Here is a partial sampling of eligible financial institutions:

ADP Retirement Services
Alliant Credit Union
Ally Bank
Ameriprise Financial
Bank of America
Betterment
Charles Schwab
Chase Bank
Citibank
Discover Bank
E*Trade
Edward Jones
Fidelity
Gainskeeper
Interactive Brokers
Merrill Lynch
Navy Federal Credit Union
Pentagon Federal Credit Union
Scottrade
Sharebuilder
T Rowe Price
TD Ameritrade
TIAA-CREF
TradeKing
USAA, USAA Federal Savings Bank
Vanguard Brokerage, Mutual Funds
Wells Fargo Bank, Advisors

I’m a fan of automatic import because it both saves time and reduces data entry errors. I did have a couple of hiccups with the import, however. I suspect that the problem is the same as I had with TurboTax – that the file is not ready for electronic import yet even though it is available in physical form. Some patience may be in order?

The Small Stuff

When entering charitable donations of physical goods, H&R Block did not provide any assistance as to valuing the object. (TurboTax and TaxACT did.)
When entering my 1099-MISC information, H&R Block quickly allowed me to indicate that it was not a business and instead a one-time event. That saved me from answering a lot of unnecessary questions.
Starting in the 2014 tax year, you’ll have to have health insurance or else pay a penalty. I indicated to H&R Block that I had employer-provided coverage for the entire year, and it did not ask for further proof or documentation.

Upselling and Price Change Tricks?
I was not presented with any upsell attempts to their Premium tier and there were no price change shenanigans, which was nice. They also had no need to offer me $40 “audit protection” because it is already included in the price. H&R Block’s “Free In-person Audit Support” is definitely a differentiating factor for the audit-fearing folks out there. In the unlikely event of an audit, an H&R Block Enrolled Agent will help you communicate with the IRS, prepare for the audit, and will attend the audit with you (though they do not provide legal representation).

The only upsell was for their “Best of Both” package, which for $50 lets you have an H&R Block human discuss and review your return with you:

H&R Block also keeps your past returns for up to 6 years for free, so there is no option to pay more for “data archiving”. Seriously, how much space on a hard drive could it possibly take?

TL;DR Recap
H&R Block did my taxes properly and covered the same topics as their competitors. I actually liked H&R Block’s Q&A format a little better than either TurboTax or TaxACT, assuming you have done your taxes online at least once or twice before; it may save you some time.

I would say that H&R Block Deluxe’s value proposition is this: it offers most of the added import conveniences of the similar TurboTax Premium, all at a fraction of the cost ($30 vs. $55 Federal, both $37 State). If you have a lot of stock sales from a specific broker, sign up for a account (they are all free to try; you only pay when you file) and go straight to the 1099 section to see if the H&R Block supports it. H&R Block also offers free in-person audit support, which costs $45 from TurboTax and $40 from TaxACT.

Bottom line: H&R Block Online offers most of the time-saving features of TurboTax for a lower price ($30 vs. $55 Federal, both $37 State), plus it includes free audit support which costs $40+ with other services.

Filed Under: Reviews, Taxes

Last updated: February 27, 2015

TaxACT Review – 2014 Tax Year Features and Screenshots

February 19, 2015 By Jonathan Ping 10 Comments

Having already done my TurboTax 2014 review, here is my review of TaxACT 2014. (H&R Block is next week.) For all three, I will be comparing the far-more-popular online versions.

Price
TaxACT come only in two basic flavors: Free and Deluxe. With the Free Edition, Federal (including e-File) is free, while State (included e-File) is $14.99. With the Deluxe Edition, Federal (including e-File) is $12.99, while State (included e-File) is $7. (The “Ultimate Bundle” is simply getting Deluxe + State for the same price of $19.99; there is no discount.) So if you do want Fed + State returns, the Deluxe bundle is only $5 more expensive than the Free bundle.

They also have a promotion where if you import a PDF copy of your 2013 TurboTax or H&R Block return, you can get TaxACT Free Federal + State for $5, a savings of $9.99 off the regular price. Similar $5 deal for US Armed Forces with qualifying EIN.

Unlike TurboTax and H&R Block, TaxACT supposedly does not base the tiers on your tax situation – for example if you have stock sales or itemized deductions. Instead, it’s more about the level of service and convenience. Deluxe includes things like telephone support, charitable donation valuation assistance, importing from previous year TaxACT returns, and importing W-2 and 1099 forms (where available).

Accordingly, I tried my best to just use the Free version, but as you’ll see below after multiple hurdles and upsell attempts, I finally gave up and upgraded to Deluxe. Note that after you agree to upgrade, there is no way to downgrade again. You have to start over with a new account and username.

Tax Situation
Here’s a quick summary of our personal tax situation.

Married filing jointly, subject to state income tax
Both with W-2 income, as well as some simple 1099-MISC forms.
Interest income and dividend income from bank accounts, stocks, and bonds (Schedule B).
Contribute to retirement accounts (401ks and IRAs).
Capital gains and losses from brokerage accounts (Schedule D).
Itemized deductions (Schedule A), including property taxes and charitable giving.

User Interface and User Experience
The 2014 user interface for TaxACT is also cleaner than in previous years. Overall I think it is just fine, but on on a relative basis it felt a little cluttered with smaller text (you can enlarge things with your browser using Ctrl+ or Command+, but then the graphics looked a little off). Everything worked without issue, I just felt more eye strain as compared with TurboTax. There will be screenshots throughout this review.

TaxACT uses the same question-and-answer format as other tax prep software. One way that they are different is that for filling out 1099-INT and 1099-DIV forms, you can use a special forms view where it looks like your actual paper form:

I liked the idea, but in practice it wasn’t that great. 1099 forms may have the same numbers but usually have different layouts from provider to provider, and their model form has spaces for information like address that you don’t even need to enter in the normal Q&A guided format. In the end, the regular way is probably faster.

Importing Data From Previous Years
If you used TaxACT the previous year, it will pull up all of your old tax information only if you upgrade to Deluxe. You’ll get filing status, dependents, address, DOB, SSN, etc. Ironically, you can also import a previous year’s return from another provider like TurboTax or H&R Block by uploading a PDF of your old return – all without upgrading to Deluxe (I guess they don’t want to put up another hurdle for potential converts). So much for rewarding loyalty!

Importing W-2 and 1099 Forms Directly From Providers
Technically, TaxACT does support some W-2 and 1099 direct imports for Deluxe users. But in reality, this feature is very limited as compared to bigger competitors H&R Block and TurboTax. The same W-2 form that I imported successfully while using TurboTax was not available on TaxACT. I got the impression that relatively few employers were supported.

TaxACT does not support 1099-INT from any banking institutions. None.

TaxACT does now support 1099-B direct imports, but only from the following six financial institutions:

TD Ameritrade™
ShareBuilder®
Form8949.com
GainsKeeper®
Raymond James®
Betterment

This is where I gave up and upgraded to Deluxe, as I wanted to test out this import feature. It worked fine, but you will need information from your paper 1099 form from TD Ameritrade and Sharebuilder, as opposed to just knowing your login information. Betterment import worked fine with just login information. You can also import via .CSV file as with other tax prep providers.

The Small Stuff

Having to input W-2 and 1099 forms manually increases the likelihood of data entry errors, and in fact I did make an error but TaxACT caught it as it didn’t make sense relative to my other numbers.
When entering my 1099-MISC information, TaxACT also led me down the same rabbit hole as TurboTax, asking the name and nature of my “business”, trying to determine if it was a hobby/farm/business, asking my business license number, and trying to claim various deductions like home office. I guess that’s just how it is done now by everyone.
Starting in the 2014 tax year, you’ll have to have health insurance or else pay a penalty. I indicated to TaxACT that I had employer-provided coverage for the entire year, and it did not ask for further proof or documentation.
When it came to the foreign tax credit, TaxACT’s questions made it easier to claim it as a credit rather than a deduction, as compared to TurboTax (it is more valuable as a credit).

Upselling and Price Change Tricks?
My goodness. The upsells with TaxACT Free were quite annoying this year, seemingly on every third screen. If you want to import a W-2, you’ll have to upgrade to Deluxe. If you want to import a 1099, you have to upgrade. If you want TaxACT to compare your tax refund if you file Married Joint vs. Married Separate, you’ll have to upgrade:

If you have more than one “Life Event” like getting married, having kids, retiring, owning a home, breathing air (ok I’m kidding on that one), then you’ll have to upgrade to Deluxe. But they don’t make it very clear that this is all just “extra guidance” and not critical to finishing your return. You could easily assume that you need to upgrade if you did any two of the things on this very broad list. Here’s the page so you can see what I mean:

The thing is, TaxACT Deluxe is still cheaper than their competitors by more than $20 if you do both Federal and State! I would say just pay the extra $5, get all the features available, and save yourself the headache of reading their spiel and saying no over and over. It’s still a good deal. If you only have a Federal return and have relatively simple needs, then out of pure cheapskate principle I might try harder to get that $0 return. 😉

The final two upsells are Tax Audit Defense for $39.99 and Data Archive Service for $6.99. I would personally decline both as I’m not sure of the quality of their subcontracted personnel and I can just save a PDF of my final return thank you very much.

TL;DR Recap
In the end, TaxACT did my taxes properly and basically asked the same questions in the same manner as their more expensive competitors. The full-featured version of TaxACT Deluxe costs at most $20 for both Federal and State returns including e-File for both. Their Free Federal version provides a full-featured free Federal return at any income level and for all tax forms. Many other providers have “free” editions that are restricted to certain income levels or are only for 1040-EZ forms with no investment income or business income.

Users should accept that the import feature set is rather weak and you will spend more time with data entry if you have multiple W-2 and/or 1099 forms, including stock sales. In addition, the repeated upsell attempts to Deluxe were a turn-off. I had to read every one carefully and decide “is it really worth the upgrade?” If I was going to pay for the State return anyway, I would have gone back in time and paid the extra $5 upfront just to avoid the hassle.

Bottom line: TaxACT is the best value choice if you just want accurate DIY tax return software and you don’t value the time-saving features of their competitors. If your return is relatively simple, why pay more than nothing (Fed only) or $20 (Fed + State)? If you are doing Federal + State returns and want to avoid repeated upsell attempts, I would pay the extra 5 bucks and upgrade to Deluxe right off the bat. You’ll still pocket some decent savings and you’ll be in a better mood. If you are converting from TurboTax or H&R Block and have a PDF copy of your 2013 return, note their $5 Fed + State deal.

Filed Under: Reviews, Taxes

Last updated: April 22, 2015

ETF Tax-Loss Harvesting: 70% Overlap Rule of Thumb for Substantially Identical

Credit Karma Tax 2019: $0 Federal and $0 State Tax Filing w/ No Last-Minute Charges

Mortgages, Imputed Rent, and Early Retirement

IRS Estimated Taxes Due Dates 2016

Pay Taxes With Credit Card: Lowest Fee Rates and Limited-Time Promotions

TurboTax vs. TaxACT vs. H&R Block Online 2016 Lightning Review

TurboTax Desktop Software 2015 Deals, 40% Off at Amazon

How To Generate and Mail Your Own 1099-MISC Forms

Home Improvement Receipts: Scan Now, Save Indefinitely

Paperless vs. Paper Statements

H&R Block Online Review – 2014 Tax Year Features and Screenshots

TaxACT Review – 2014 Tax Year Features and Screenshots

Popular

Site Search

Contact Me

Most Visited (Last 48 Hours)

Recent

Categories

Archives

Categories

Advertiser Disclosure

Share this:

Share this:

Share this:

Share this:

Share this:

Share this:

Share this:

Share this:

Share this:

Share this:

Share this:

Share this:

Popular

Site Search

Contact Me

Most Visited (Last 48 Hours)

Recent

Categories

Archives

Categories

Connect with me

Advertiser Disclosure